December 4 to 6 and December 11 to 13 The festive Annapolis Holiday Market showcases about 150 local and regional artisans, offering a wide array of crafts, handmade gifts, and specialty holiday foods. Visitors can savor seasonal treats like hot chocolate and spiced wine while enjoying live entertainment and the festive holiday spirit of Annapolis. This is one of the premier holiday markets in the region and has something for everyone to enjoy. Free admission and free parking. Make it a holiday weekend to remember in Annapolis, Maryland. Tour buses welcome.